Penicillin salt of hydroxy-menaph-thyl-piperidine



Patented Apr. 7, 1953 PENICILLIN SALT OF HYDROXY-MENAPH- THYL-PIPERIDINE Harley W. Rhodehamel, Jr., Indianapolis, Ind.,

assignor to Eli Lilly and Company, Indianapolis, Ind., a corporation of Indiana No Drawing. Application February 13, 1952, Serial No. 271,445

This invention relates to a novel penicillin salt and the preparation thereof.

I have discovered that Z-hydroxy-l-piperidinomethyl naphthalene or its salts can be combined with penicillin or its salts by neutralization or metathetical reactions to form a sparingly soluble penicillin salt, thereby affording a means of precipitating penicillin from solution, and of purifying penicillin. Moreover, the novel penicillin salt can be utilized therapeutically. A prolonged penicillin blood level can be secured upon administering the salt parenterally by methods known to the medical art.

The following examples illustrate the preparation of the novel salt of this invention:

Example 1 To a solution of 0.3 g. of penicillin (e. g. a commercial mixture of the several penicillins) dissolved in 1.8 ml. of amyl acetate are added 0.3 g. of 2-hydroxy-1-piperidinomethylnaphthalene dissolved in m1. of amy1 acetate. The mixture is cooled and stirred occasionally whereupon the 2-hydroxy-1-piperidinomethylnaphthalene salt of penicillin precipitates. The salt is isolated as by decantation or filtration, and dried in vacuo.

The salt is represented by the following formula in which P represents penicillin:

CHPC H:

CHz-N CH2 P CH2-C 1 2 Claims. (01. 260-2391) Example 2 To an aqueous solution of 2 g. of the potassium salt of penicillin G in 15 ml. of water is added a solution of 2 g. of Z-hydroxy-l-piperidinomethylnaphthalene hydrochloride in ml. of water. The mixture is cooled and stirred occasionally whereupon the slightly soluble Z-hydroxy-l-piperidinomethylnaphthalene salt of penicillin G precipitates. The salt is separated, and dried in vacuc.

I claim:

1. The 2-hydroxy-1-piperidinomethylnaphthalene salt of penicillin represented by the follow- 'ing formula in which P represents penicillin:

CHr-CHg CHr- CH2 2. The 2-hydroxy-l-piperldinomethylnaphthalene salt of penicillin G.

HARLEY W. RHODEHAMEL, JR.

No references cited. 

1. THE 2-HYDROXY-1-PIPERIDINOMETHYLNAPHTHA LENE SALT OF PENICILLIN REPRESENTED BY THE FOLLOWING FORMULA IN WHICH P REPRESENTS PENICILLIN: 